Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer

Autores
Brito, Gilmar A.; Sarotti, Ariel Marcelo; Wipf, Peter; Pilli, Ronaldo A.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.
Fil: Brito, Gilmar A.. Universidade Estadual de Campinas; Brasil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Wipf, Peter. Univeristy Of Pittsburgh; Estados Unidos
Fil: Pilli, Ronaldo A.. Universidade Estadual de Campinas; Brasil
Materia
Cascade Cyclization
Imine
Formal Synthesis
Stemoamide
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/5987
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/5987
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimerBrito, Gilmar A.Sarotti, Ariel MarceloWipf, PeterPilli, Ronaldo A.Cascade CyclizationImineFormal SynthesisStemoamidehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.Fil: Brito, Gilmar A.. Universidade Estadual de Campinas; BrasilFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Wipf, Peter. Univeristy Of Pittsburgh; Estados UnidosFil: Pilli, Ronaldo A.. Universidade Estadual de Campinas; BrasilElsevier2015-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5987Brito, Gilmar A.; Sarotti, Ariel Marcelo; Wipf, Peter; Pilli, Ronaldo A.; Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer; Elsevier; Tetrahedron Letters; 56; 48; 10-2015; 6664-66680040-4039enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403915302148info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2015.10.017info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:28:45Zoai:ri.conicet.gov.ar:11336/5987instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:28:46.15CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
title Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
spellingShingle Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
Brito, Gilmar A.
Cascade Cyclization
Imine
Formal Synthesis
Stemoamide
title_short Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
title_full Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
title_fullStr Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
title_full_unstemmed Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
title_sort Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer
dc.creator.none.fl_str_mv Brito, Gilmar A.
Sarotti, Ariel Marcelo
Wipf, Peter
Pilli, Ronaldo A.
author Brito, Gilmar A.
author_facet Brito, Gilmar A.
Sarotti, Ariel Marcelo
Wipf, Peter
Pilli, Ronaldo A.
author_role author
author2 Sarotti, Ariel Marcelo
Wipf, Peter
Pilli, Ronaldo A.
author2_role author
author
author
dc.subject.none.fl_str_mv Cascade Cyclization
Imine
Formal Synthesis
Stemoamide
topic Cascade Cyclization
Imine
Formal Synthesis
Stemoamide
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.
Fil: Brito, Gilmar A.. Universidade Estadual de Campinas; Brasil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Wipf, Peter. Univeristy Of Pittsburgh; Estados Unidos
Fil: Pilli, Ronaldo A.. Universidade Estadual de Campinas; Brasil
description A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/5987
Brito, Gilmar A.; Sarotti, Ariel Marcelo; Wipf, Peter; Pilli, Ronaldo A.; Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer; Elsevier; Tetrahedron Letters; 56; 48; 10-2015; 6664-6668
0040-4039
url http://hdl.handle.net/11336/5987
identifier_str_mv Brito, Gilmar A.; Sarotti, Ariel Marcelo; Wipf, Peter; Pilli, Ronaldo A.; Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer; Elsevier; Tetrahedron Letters; 56; 48; 10-2015; 6664-6668
0040-4039
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403915302148
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2015.10.017
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1846781868389695488
score 12.982451

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